Tuscan Towns Beyond the Main Cities

Why go

Cortona and Lucignano favour hill streets and views, while Fiesole gives a panorama back to Florence. Pitigliano and Sorano reveal southern Tuscany’s tuff landscape; San Gimignano is shaped by its medieval towers. Use these as regional choices, not a single route across Tuscany.

What to look for

• Cortona’s Val di Chiana outlook and Lucignano’s ring streets
• Pitigliano and Sorano’s tuff-cliff settings
• San Gimignano’s tower skyline

Useful to know

• Choose an area first; these towns span several provinces.
• Allow extra time for steep streets in hill towns.

The route, stop by stop

1. 01

   Optional · – min

   Cortona

   Cortona climbs steeply above the Val di Chiana, pairing broad views with Etruscan remains and medieval streets. Allow time for the slope if you want to explore beyond the main street.

   Explore

2. Walk · 334 min · Estimated

   02

   Optional · – min

   Lucignano

   Lucignano is a small walled Valdichiana town built in elliptical rings. Its street plan, more than any single monument, makes it rewarding to explore on foot.

   Explore

3. Walk · 1207 min · Estimated

   03

   Optional · – min

   Fiesole

   Fiesole sits above Florence, combining a city panorama with Etruscan and Roman remains. It suits a hill-town excursion when you want to see Florence from outside its centre.

   Explore

4. Walk · 2319 min · Estimated

   04

   Optional · – min

   Pitigliano

   Pitigliano rises almost vertically from a tuff ridge in southern Maremma. The cliffside view, old centre and Jewish history make it a substantial stop.

   Explore

5. Walk · 1836 min · Estimated

   05

   Optional · – min

   San Gimignano

   San Gimignano's surviving medieval towers make its hilltop skyline distinctive, while the streets inside the walls reveal churches, civic art and a former pilgrimage stop.

   Explore
6. 06

   Optional · – min

   Province of Arezzo

   Arezzo and Cortona contrast a city of churches and frescoes with a hill town above the Val di Chiana. Lucignano adds a smaller medieval street plan.

   Explore
7. 07

   Optional · – min

   Province of Florence

   Beyond Florence, Fiesole and Certaldo offer two different hill-town walks: one looks back toward the city, while the other leads through the walled streets of Certaldo Alto.

   Explore
8. 08

   Optional · – min

   Province of Grosseto

   Southern Tuscany pairs Maremma’s coastal and lagoon landscapes with dramatic inland tuff towns. Grosseto and Orbetello serve different settings; Pitigliano and Sorano shift the visit uphill.

   Explore
9. 09

   Optional · – min

   Province of Livorno

   The Livorno area gives Tuscany a Tyrrhenian face: the port city’s Venezia district contrasts with Bolgheri’s cypress approach, village lanes and wine-country setting.

   Explore
10. 10

    Optional · – min

    Province of Lucca

    The Lucca area reaches from Garfagnana’s small historic centres to Pietrasanta’s sculpture-filled square. Barga and Castelnuovo di Garfagnana make useful mountain-side choices.

    Explore
11. 11

    Optional · – min

    Province of Massa and Carrara

    Carrara’s marble-faced centre contrasts with the medieval streets of Pontremoli and Fivizzano farther inland. Pick a coastal-side city or a Lunigiana town for a focused walk.

    Explore
12. 12

    Optional · – min

    Province of Pisa

    Pisa’s wider province includes hill towns with different strengths: San Miniato for a ridge walk, Volterra for layered walls, and Vicopisano for a quieter town setting.

    Explore